


Set my Midnight Sorrow Free

by orphan_account



Series: 28 Days of Sterek [10]
Category: Teen Wolf (TV)
Genre: 5+1 Things, Boys Kissing, Flirting, Love Confessions, M/M, Oblivious Stiles and Derek, Pining Derek, Romance
Language: English
Status: Completed
Published: 2016-02-13
Updated: 2016-02-13
Packaged: 2018-05-20 02:09:28
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,013
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5988490
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Five times Stiles flirted with someone other than Derek and the one time they finally realized what really should be happening.</p>
            </blockquote>





	Set my Midnight Sorrow Free

**Author's Note:**

> idek

1.

Stiles was known to become close to people very fast. Most of the time he didn't respect the term personal space and wouldn't hesitate to practically lay on top of them. Derek thought him and Stiles were finally becoming close after one rainy night they were cuddled up on Stiles' couch watching a movie. But then Derek started to notice things- Stiles would flirt with other people right in front of him. And even if they were becoming closer, he never flirted with Derek.

Derek first noticed it when he was dragged to watch one of Stiles and Scott's lacrosse games with the rest of the pack. They were far away from the bench of players but Derek's werewolf hearing picked up a conversation between Stiles and Danny.

"Dude!" Stiles said as he plopped down onto the bench next to the goalkeeper. "That was an amazing save!"

Danny gave Stiles a bright smile. "Thanks, Stiles." But Stiles didn't stop there.

"Seriously though, we would be down like seven points if it wasn't for all your great saves tonight. You have amazing reflexes."

Excuse him, Derek had amazing reflexes. Better than Danny that's for sure. He didn't hear the rest of the conversation over the millions of thoughts running through his head. But Derek did catch the faint blush on Danny's cheeks and the smile that never left Stiles' face. It pained him, physically pained him to see the two interact. Danny was the only other known openly gay student in Stiles' grade besides Stiles himself plus the dude was insanely sweet and attractive. Once Derek thought about it, why wouldn't Stiles be in to Danny? He should've seen it coming honestly.

"I can smell the jealousy coming from you," Isaac whispered in Derek's ear with an amused tone. Derek just flashed his red eyes at the beta with a quiet growl which immediately caused the sly grin to wipe off of Isaac's face. They didn't speak of Stiles the rest of the game.

2.

Derek was relieved when he found out Stiles was in fact not planning to woo Danny and vice versa. Turns out Danny was actually dating Ethan now and while Derek didn't exactly love the twin, he was happy for them.

His joy was cut short during training the next day in the forest next to the Hale house. It was Boyd vs. Isaac and they seemed to be evenly matched. The rest of the pack was standing to the side of the sparring, some sitting on the black steps. Derek observed his betas carefully and was impressed with how much they've improved over time.

Boyd eventually caught Isaac when he was distracted and pinned him to the ground with both hands. Derek called the match to be over and for the next two to step up. Once Boyd walked back to the group Stiles immediately stood up and laid a hand on the man's arm.

"You did great Boyd, congratulations," Stiles praised him. Boyd just gave Stiles a small smile and a thanks, knowing the feelings Derek had for the human. "You're so strong, dude. Like please teach me your ways of how you get your biceps so big." He further proved his point by giving a squeeze to Boyd's arm and rubbing it a little. Derek fumed from across the clearing and even Erica wasn't looking away, even after Cora pushed her to the ground. Looks like Derek wasn't the only one getting jealous.

Boyd just brushed Stiles off with an awkward smile and moved to sit near Isaac. No one said anything about the encounter to Stiles, who just retook his seat and acted like he hadn't just flirted with one of his fellow pack members.

And if Derek purposefully made Boyd spar him next just so he could defeat the guy to impress Stiles, well, no one has to know.

3.

Derek was furious when he pulled up in his car to his loft building only to hear loud music and see flashing lights coming from his home. He stomped up the stairs and threw open the door. Sure enough, there was a huge party of God knows how many people all painted and glowing under a black light. Derek pushed through the crowd, yelling at people as he went. But no one paid any attention to the alpha or even heard him over all the people and music. 

Derek decided to try and find Scott first, he'd know what was going on here. Derek faintly got his scent from across the room with great difficulty due to the dozens of sweaty bodies around him. Derek also caught another scent coming from the opposite side, one he'd never forget. 

When he turned Derek saw Stiles sitting on the spiral staircase, shirt glowing and illuminating his features beautifully. But next to him sat a girl in a fluorescent wig with bright orange lipstick. They were too close for Derek's liking. He stalked a little closer to try and see what they were saying and Derek just managed to make out the words "beautiful" and "funny" coming out of Stiles' mouth. By the way the girl ducked her head bashfully Derek guessed Stiles was swooning her with his magnificent way with words. He didn't want to see this so he left to find Scott again.

On his way there he was stopped by a dancing Isaac and Allison. He really didn't need to see them both without shirts making out but he needed answers as to why there were all these strangers partying in his loft. 

"Isaac!" Derek pulled the beta away from the huntress. Isaac looked up to Derek with a slight nervous look in his eyes like he'd just been caught with his hand in the cookie jar. "Wanna tell me what the hell is going on?"

"I promise it wasn't my fault! It was Ethan's!" Isaac rushed out and held up his hands in mock defense. Derek growled under his breath. Ethan wasn't even part of his pack yet he'd thrown a party in Derek's home.

"I'm going to kill that son of a bitch." Derek started to walk away but Isaac stopped him with a hand on his arm, lowering his voice so Allison couldn't hear them.

"He did it for Danny, Derek. You should've seen the look on Danny's face," said Isaac. "You'd do the same thing for Stiles if it meant seeing him so happy."

Derek pulled his arm out of Isaac's grip harshly and stormed away without replying. He couldn't help himself and looked in Stiles' direction again. The girl was even closer to him now and he pressed a kiss to her cheek. But the bright smile Stiles let out after she said something made Derek's insides feel funny. Isaac was right, he would do it in a heartbeat for Stiles if it meant getting that reaction out of him.

4.

The next time Stiles charmed someone with his looks was completely unexpected. Now Derek had not witnessed this one but Scott and Isaac made sure to explain it later in full detail.

Mr. Harris had assigned a very important essay to his class a while ago that was due that day. Stiles forgot to turn his in and after class he asked to speak to Mr. Harris. Scott and Isaac waited outside of the door, listening in on what was happening inside of the classroom.

"Mr. Stilinski, I assume you've come up with a completely ridiculous and impossible excuse as to why your semester essay isn't on my desk?" Harris asked in that sarcastic, asshole-ish form he always did.

Stiles put on his most apologetic look and stood in front of Harris' desk. "I'm really sorry Mr. Harris. Is there any way I can get an extension?"

Everyone knew Mr. Harris was not one to bend the rules for any student, especially not one he despised as much as Stiles. "That's funny. I could've just sworn I heard you ask for an extension."

Stiles cursed himself in his head for what he did next (or so he told Scott after the whole thing) and tried not to throw up in his mouth as he leaned over the desk and put his head in his hands. Harris just stared at the boy confused and slightly shocked.

"Please sir," Stiles said in a lowered voice and he made sure to stick out his bottom lip. Lydia always told him he had the best sad puppy face. "Everything's just been so hectic lately and I promise I'll get it into you by the end of the week." He even went as far to bite his lip and stick his butt out a little more than usual. 

"I-I can't make exceptions," Harris stuttered and inside his head Stiles grinned triumphantly while also feeling like crawling in a dark hole and not coming out for the next million years.

Stiles leaned even closer and put a desperate hand on Harris' arm. "Please? I won't let you down this time. I'm sure a brilliant and...considerate man like yourself can understand?" He slapped on a sweet and innocent smile.

Harris looked to the hand on his arm before stating back up at Stiles. Then the teacher rapidly shot up from his desk, face twisted in both anger and what looked like confusion. "You have until Friday afternoon." Harris pointed towards the door. Stiles thanked him and skipped confidently out the door.

Scott and Isaac just stared at the guy. "What the hell was that?" Scott said dumbfounded.

Stiles laughed and shrugged but still held a disgusted look on his face at the same time. "Boys gotta do what a boys gotta do. But I'm just gonna go home and gage my eyes out."

5.

Life continued on with Derek ignoring the growing feelings he was having for the human boy. Apparently though he wasn't that good at hiding it and Erica approached him after a pack meeting on day. "It's starting to get pathetic Derek," she said.

He sighed, not even bothering to snap at the girl because he knew she was right. "Well, what am I supposed to do? He's been flirting with literally everyone but me, even a goddamn teacher. I don't exactly think I have a chance."

Erica closed her eyes and put a hand to her forehead in frustration. "You both are so oblivious wow." She left without explaining what she meant which made Derek very confused.

He rejoined the rest of the pack and stood next to Stiles without even thinking about it. He just offered Derek a small smile, nothing compared to what he'd been showing so many other people recently.

"We were thinking it'd be a good pack bonding idea to go out to a club tonight," Scott filled him in. Derek's eyebrows shot up in surprise. They usually all just ordered pizza or had a movie marathon but now they actually wanted to go out?

"What do you say Derek?" Stiles asked him. There was nothing behind the words no matter how hard Derek tried to see it. Stiles just treated him like a friend, a mere acquaintance. But Derek still couldn't say no to those beautiful brown eyes. 

So that's how Derek found himself an hour later, pressed into a booth with his pack in the Jungle, even though him and Stiles were the only homosexuals in the group. Something smelled fishy.

"Come on guys, let's dance!" Lydia exclaimed to the group, pulling up Allison who pulled Isaac who pulled Erica and so on. It left with Stiles trying to get Derek to come with them.

"Uh, I better stay here to guard the table," Derek said. Stiles gave him an 'are you kidding me look'. "Plus I don't dance."

"Party pooper." Stiles left with his arms crossed to join the partying pack on the dance floor. Derek decided admiring his crush's dance moves from afar was better than embarrassing himself.

Two songs later and the pack split up. Derek lost track of all his betas and pack members but he didn't care, he was still entranced by the fluid sways of Stiles' hips. He felt his claws start to come out though when a man approached Stiles and whispered in his ear. Stiles said something back to the guy, this time loud enough for Derek to pick up since they were fairly close to the table.

"You're not so bad looking yourself big guy," Stiles replied. Derek assumed the guy had complimented Stiles on his appearance. The stranger was not subtle at all as he moved his eyes down Stiles' body, stopping at his still moving hips. Stiles noticed as well as Derek and the human seemed to become more wary of this strange man coming onto him.

"You're an amazing dancer, I've been watching you from the bar," stranger said. Derek didn't even flinch when he punctured an empty soda can with his sharp claws.

"Uh, thanks," Stiles said while slowly inching away. "You are too." It came out more like a question than a compliment.

Then the guy placed his hands on Stiles' hips and pressed their groins together. This made Stiles try and push the man away but he wouldn't budge, he just smirked and placed his head in the crook of Stiles' neck. "Get off of me."

Derek felt his growl come out and was thankful for the loud music to hide it. He abruptly stood up from the booth, shaking a couple glasses, and walked towards the two on the dance floor. Derek practically ripped the guy off of Stiles and shoved him back. Stiles immediately ducked behind Derek's protective stance.

"He told you to get off," Derek sneered. 

The man just laughed. "Hands off tough guy, I got this hot piece of ass first. But hey, if y'all are up for a little threesome action later you are extremely hot as well." The creep winked at Derek and the alpha snapped. No one talked about Stiles that way. He let his eyes grow red as a deep growl escaped his throat. The man's eyes went wide with shock and he scampered away in fear. 

Derek turned around only to be met with Stiles' arms around his torso. "Thank you Derek," he said sweetly.

Derek just hugged the boy back knowing he may not get a lot of chances to do it in the future. "I wasn't going to let that pervert touch you. I can smell him all over you and it's bothering me."

Stiles leaned back and looked into Derek's eyes. Derek saw him visibly take a deep breath before shyly saying. "Well why don't you fix that then?"

Derek raised an eyebrow at Stiles and wondered if he was serious. But the human just smiled and nodded which was all it took for Derek to insert his face into the crook of Stiles' neck and rub his scent all over him. It felt good, it felt right to make Stiles smell like him. Stiles should always smell like Derek.

+1.

Nothing was the same after that night and Derek didn't know why. Stiles was starting to talk to him more, drop more hints of how he loved Derek's leadership or humor or smile. It was weird as Stiles used to never say anything of that sort to Derek before.

"He's acting weird," Derek told Erica after he'd explained his observations to her.

"You are so blind," was Erica's reply.

"What?"

"Derek! Stiles is into you!"

Derek gave her an incredulous look. "What? No he's not." He couldn't be.

"You even said yourself that Stiles is flirting with you more now-"

"Well, I didn't exactly say flirting."

"-shouldn't that tell you something? Also even before now I've seen the way he looks at you when you aren't looking. It's the same way I catch you looking at him."

Derek stared at her in shock. Was Stiles actually into him? Was it even possible?

"Now please stop brooding in the corner and go get him!"

Derek didn't know why but he followed Ericas advice. What's the worst that could happen? If he didn't just man up and tell Stiles how he felt then he'd go on wondering what would've happened if he did. 

Derek didn't mean to scare Stiles but felt the window was easier access to the boys room. Once he dropped into the bedroom the human jumped about a foot out of his desk chair.

"Derek? What the hell dude?!"

Derek couldn't hold it in any longer and had to spit his feelings out before he lost confidence. "Please let me get this all out before interrupting. Stiles I have liked you for a very long time. I mean, like like you. God, I sound like a stupid teenager with a crush. But every little thing you do makes me fall for you more and more every day. I've seen you flirting with everyone recently and its hurt because I felt I was the one person you didn't. But after that night at the Jungle I've been noticing the little things you slip into our conversations and its given me some hope that I won't leave today completely rejected and heartbroken."

Stiles' mouth was open like a fish once Derek finished his rant. He didn't say anything, just stood up and jumped in the werewolf's arms to press a firm kiss to Derek's lips.

"I like you too Derek," Stiles said once they broke apart. "I never flirted with you because you made me nervous, still do. But after you saved me from that guy at the Jungle and held me I knew I shouldn't be afraid anymore so I started dropping things to make it obvious. I'm glad it worked."

Derek beamed at Stiles and kissed him again, this time more passionately. He couldn't believe he finally got to hold Stiles in his arms and taste what it felt like to kiss him. Stiles still smelled like Derek and it was perfect. He was perfect.

**Author's Note:**

> please leave a comment and kudos if you enjoyed! also requests are open so please comment what you want me to write because I really need more creative ideas :P


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